When my wife had been in labor for 16 hours, I played her John Prine’s “Everything Is Cool.” She’d begun gasping instead of breathing, climbing into the tub to gather herself. As Prine’s fingerpicking rang out from a tiny speaker, she closed her eyes and smiled.

The song is simple, like all Prine songs, a folk lament with a deliberate pace ideal for slow breathing. Over three chords, the singer-songwriter pines for a loved one who has traveled beyond reach—“Across the sea to an island where the bridges brightly burn/So far away from my land/The valley of the unconcerned.” The valley of the unconcerned—that felt like where our daughter was at that moment. We were stuck somewhere else, whatever you would call such a place: the cul-de-sac of the flustered. Together, we beckoned her: join us. The song looped, my wife’s labor progressed, and our daughter slowly moved closer. The midwife and nurses gathered around my wife, and she started pushing. Everything is cool.Everything’s OK.

When my daughter died two years later, the song rang out again into the stricken silence at her service. This time, it felt like a hymn. The song is pierced halfway through by an image of grace and purification: “I saw a hundred thousand blackbirds just flying through the sky/And they seemed to form a teardrop/From a black-haired angel’s eye/And that tear fell all around me/And it washed my sins away.” A message from our daughter, perhaps, a dispatch from the valley of the unconcerned, to which she returned. Everything is cool here, guys, she was reassuring us. Everything’s OK.

I tell all of this to John Prine, and he listens gravely, attentively. His wife Fiona has just brought me into his Manhattan hotel suite and left us alone. “Well, since you’ve been through what you’ve been through, you deserve to know what the song is about,” he says, his voice so gravelly it sounds broken up by radio static. “It wasn’t about death, so much as about the death of a relationship. You just met the ‘black-haired angel,’” he says, nodding in Fiona’s direction. “I met her chasing after my soon-to-be ex-wife. I had malice in my heart, as angry as I could be, like I was going to find somebody and hurt them. It wasn’t like me at all; I wanted to get rid of that feeling. And while I was running around after my ex, I ran into Fiona, and she washed my sins away. I don’t know if I ever told her that. I think she knows it though.”

I ask if it surprises him that his divorce song would be my death song, that it would speak to me so clearly of grief and grace, redemption and transfiguration. He thinks for a second, then smiles. “Well, there’s only two things,” he says. “There’s life, and there’s death. So it’s a 50/50 shot.”

Prine performing “Everything Is Cool” in 1992

My wife grew up with John Prine. Even after her parents divorced, angrily and at length, they would check in when he released a new album. I had barely heard of him, and my mother-in-law, shocked at my ignorance—“aren’t you supposed to be a music critic?”—urgently pressed two of his songs upon me.

The first was “Hello in There,” a tender, perceptive song about the loneliness and indignity of old age that Prine somehow wrote when he was 23 years old, when he was a mailman humming tunes to himself. It’s one of three songs he sang at an open mic night in Chicago for his first-ever performance in 1970. When he finished, the crowd went silent, and at first he thought he must have done something wrong. Then they started applauding. Soon after that, he had a record deal with Atlantic. He quit the post office.

The version my mother-in-law wanted me to hear, though, wasn’t the 1971 studio version. It was from 2001, when Prine was in his fifties, his already sandpapery voice further degraded by throat cancer followed by radiation and surgery. Suddenly a tender song peeking into the heads of the elderly became a first-person testimonial, an unlikely youthful flash of insight ripening into lived experience. The ability to write this song at the age of 23, and then sing it for 30-plus years, seemed to split the difference between empathy and telepathy. I was transfixed.

The other song my mother-in-law sent me was “Everything Is Cool.” Four years before my daughter died, “Everything Is Cool” also played at my father-in-law’s funeral, where I sat next to my wife and mother-in-law. They started crying openly as the song rolled out over the crowd. By now, the song couldn’t be any closer to me than my breath in my chest.

Prine performing “Hello in There” in 2001

I’m not unusual or notable among Prine fans—most have had one of his songs at their side at a profoundly intimate moment. “It’s a familiar story, actually,” Prine remarks, when I tell him how I discovered him. “It’s a big part of how my music has gotten around since I got started. A lot of it had to do with families—car trips and sing-alongs. Some people told me it was the only thing that their family did as a family. It would’ve been nice to be like the other boys and girls and have a hit, you know, but it’s more honest to have your music passed down through families and friends and loved ones. I’m proud of it. ”

Prine has been steadily and quietly accruing diehards like me for his entire career. At the outset, he was a Chicago phenom, a local hero, and thus had weird champions for a country or folk artist: Roger Ebert famously wrote the first piece on him, and John Belushi kept nagging “Saturday Night Live” to book him. His songs have been covered by everyone: Bette Midler, Bon Iver, Johnny Cash, Bob Dylan.

Prine grew up in the Midwest, and his songs are full of very white, Middle-American sounding folks, people with names like Donald and Lydia and Loretta and Davy who drive trucks and serve in the Marines. But he doesn’t fetishize the lives of those he grew up around, or blow them up into gaudy myth like Springsteen. The people in his songs are never allegories for his own thoughts; they are just people, living with their own complications, and Prine takes pains to get them just right. In his songs, life is one long exercise in ambivalence, and the only honest point of view is a squint.

Prine and I are talking in part because he has just released his first album of new songs in 13 years. It is called The Tree of Forgiveness, and there are hints of a wry, skeptical soul reckoning with the idea of an afterlife. The final song is called “When I Get to Heaven,” and it paints the beyond as the place you can misbehave all you want, fulfill every desire—drink and eat as much as you like, and take off your wristwatch, because “what are you gonna do with time after you’ve bought the farm?” In the chorus, Prine smokes a cigarette “nine miles long” with palpable relish.

“If there is a heaven, and I’m going there, that’s the way I want it,” Prine tells me, grinning. He quit smoking after his first bout with cancer in 1997, but he never lost his taste for it: “I got to thinking, Where am I gonna have that cigarette? Well, in heaven. There couldn’t be any cancer there, and why would they have ‘No Smoking’ signs in heaven?”

Prine’s idea of the afterlife seems much like his view of Christianity writ large: pretty good, not bad, but with room for improvement. “I can’t really sit around and talk with people who believe that the Bible is the way it happened, because that’s man-made,” he says. “I’m a writer, too; that’s how I look at the Bible. Like, ‘I could’ve written a better version than that,’ you know? At least a more interesting one, and then maybe more people would go to church. I could definitely do a revamp.”

Listening to the album, I hear an unbroken thread running all the way back to the beginning of his catalog. From “Hello in There” to 1978’s “Bruised Orange,” about an altar boy Prine saw struck by a train; from the young girls’ bodies washed ashore in “Lake Marie” to the joky “Please Don’t Bury Me,” where he requests that the deaf be given both of his ears, “if they don’t mind the size”; from the “rainbow of babies draped over the graveyard” in “He Was in Heaven Before He Died” in 1975 through to “When I Get to Heaven”; Prine has always gazed at death a little differently than everybody else who writes about it. He might not have written “Everything Is Cool” from within the grip of death, but I heard something real in it, evidence of a worldview perched somewhere between fatalistic and serene.

Death, it turns out, is ideally suited to Prine’s narrative gifts: He is sanguine, a little doleful, funny, and then so poetic you might topple over. He wrote about the crucifixion with the same understatement he brought to the train hitting the altar boy: “I’m a human corkscrew and all my wine is blood/They’re gonna kill me, mama/They don’t like me, bud.” His touch is light as his tongue is sharp, and he gets away with just about anything because he’s so genial.

“I guess I just process death differently than some folks,” he admits. “Realizing you’re not going to see that person again is always the most difficult part about it. But that feeling settles, and then you are glad you had that person in your life, and then the happiness and the sadness get all swirled up inside you. And then you’re this great, awful candy bar, walking around in a pair of shoes.”

I ask him if he ever talks to the dead people in his life. He tells me his mother sometimes comes to him as a red bird. He saw her two months ago, when he and Fiona moved into a new house. He was parked out front, and “all of a sudden I see a red bird flash by the car. I said, ‘Hey ma, how you doing.’ I knew she was checking out my new abode.”

She’s done the same thing in other places, he says. “I remember the last house I lived in, I was standing by the kitchen sink about three days after moving in. Red bird lands right on the windowsill, looks at me, checks me out, takes off. Could be a coincidence, but wouldn’t it be nice to think it’s something else?”

Photo by Danny Clinch

My wife got pregnant with our son six months after our daughter died. We started thinking about a song for him. The problem seemed almost theological, beyond the range of human capacity. It had to be something tinged with grief, but still hopeful. Something true. Early on in the pregnancy, I tried “Here Comes the Sun” (“It’s been a long cold lonely winter/It feels like years since it’s been clear”). When he was overdue and we were waiting for him, I sang him “Goodbye Yellow Brick Road” (“When are you gonna come down? When are you going to land?”).

I finally settled on another Prine song, “In Spite of Ourselves.” The song is a duet between Prine and Appalachian folk singer Iris DeMent. He is wry, croaky, and barely tuneful; she sounds like someone’s loopy aunt. The verses are nothing but dirty jokes. But the chorus feels like another message from the beyond, putting words to a vast, nameless feeling. “In spite of ourselves, we’ll end up sitting on a rainbow,” they sing. “Against all odds, honey we’re the big door prize.”

My son was born in a blind rush, 12 days late, nothing like my daughter’s slow, patient buildup. He was in our arms, squalling with his eyes shut, before we could collect ourselves. We clutched one another as if we had all been shot out of a cannon. As his face went scarlet, I leaned over and shakily sang the chorus of “In Spite of Ourselves.” He quieted, slowly and by degrees, just as I reached the end. The last line is the kind of promise that you can’t technically keep, more prayer than promise: “There won’t be nothing but big old hearts dancing in our eyes.”